Nickel-Catalyzed Desulfurative Cross-Coupling of Aryl Iodides with Heteroaromatic Thioethers via C–S Bond Cleavage

Herein, we present a Ni-catalyzed direct cross-coupling of heteroaromatic thioethers with aryl iodides via selective C­(sp2)–S bond cleavage under reductive conditions, thereby providing various biaryl frameworks with high efficiency. Mechanistic studies suggested Mo­(CO)6 played a crucial role in f...

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Veröffentlicht in:Journal of organic chemistry 2024-09, Vol.89 (17), p.12001-12009
Hauptverfasser: Zhu, Pingliang, Zhao, Yu, Ling, Shaowen, Xu, Baolong, Liu, Hui, Li, Xinjin, Sun, Feng-Gang
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, we present a Ni-catalyzed direct cross-coupling of heteroaromatic thioethers with aryl iodides via selective C­(sp2)–S bond cleavage under reductive conditions, thereby providing various biaryl frameworks with high efficiency. Mechanistic studies suggested Mo­(CO)6 played a crucial role in facilitating the activation of the C­(sp2)–S bond. This protocol demonstrated a wide substrate scope, operational simplicity, and good functional group compatibility. Furthermore, the utility of this reaction was highlighted by facile scale-up and sequential modification of heteroaryl frameworks.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00678